Holiday rentals in Highland

Cozy, Private Garden Apt in Derwood-La Belle Vie

Spacious one bedroom basement apartment. Private entrance, full bathroom and kitchenette all newly done. Freshly landscaped slate patio with garden and pond. The sound of running water provides a relaxing environment. Secluded back yard backs up to beautiful woods. 5 min away from bike trails. Large, open living space with sectional couch, and attached eating area with a table that can double as a work station. Centrally located in Montgomery County-approx 40 minutes from DC/Baltimore/Frederick.

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

Private guest suite in a newly remodeled home

We welcome you to a spacious and private basement apartment with its own entrance and self check-in. Get cozy with your guests in a space that has a bedroom with a king-size bed, an 85-inch smart TV, soft sectional , private toilet, bathroom and kitchenet, all in the same space. None of the amenities are shared. The fully-equipped kitchenet has everything you'll need to cook and warm your meals. Guest suite is the entire basement apartment which is a part of a bigger home where host lives.

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool (weather permitting) and adjacent walking trails.

Cozy Historic Guest House

Located in the heart of Old Ellicott City! This studio is warm, cozy and decorated with almost all vintage furnishings to pay tribute to the 1800s home. The space offers a well stocked bedroom, full bathroom and kitchenette. Relax on the patio or walk to the many cafes and shops on Main Street. Parking is included. The home is built into a hill so you will need to walk up a series of steps in the back from the parking area to enter. Due to this our home may not be ideal for everyone.

Cozy Retreat: Immaculate Clean, private place

Welcome to your Squeaky clean home! This neat & tidy room boasts a fully equipped kitchen, a clean bathroom with shower all for your exclusive use. You only share a wall with the main house. Ideal for solo travelers, couples or small families seeking an unforgettable getaway. Conveniently located on the corner for easy parking and access, it's situated in the most peaceful neighborhood and near metro and train stations for added convenience.Enjoy your time.

Family Vacation Home Base

Your entire family will truly enjoy the convenient access to a wealth of attractions from our centrally located home! This prime spot makes it easy to plan exciting day trips to vibrant cities such as Washington, DC, Baltimore, and Annapolis, as well as historical sites like Gettysburg. If you love the outdoors, you'll also find numerous beautiful parks and scenic hiking trails nearby, perfect for exploring nature and creating lasting memories.

Fox Cottage *Pet Friendly*

Fox Cottage is a modern addition to our 115 year old Victorian home. It’s a One Bedroom Queen size mattress & memory foam topper. There’s a Loft with a Full Size Memory Foam Mattress. The loft is a cozy space accessible by a vintage wooden ladder. It is not appropriate for people who cannot climb a ladder. There’s an outdoor seating area with a Chiminea to light a fire, enjoy a cup of coffee or wine, work or just listen to the birds.

The Duchess of Font Hill {a tiny house}

This charming 525 square foot tiny house is nestled back in Font Hill, an amazing and sought after Howard County neighborhood. It sits at the end of a driveway at a single family dwelling. 3 miles from Historic Ellicott City, Turf Valley Resort + Spa, Merriweather Concert Pavillon. BWI airport is about 25 minutes away, and Baltimore City is 30 minutes from our home. 1 queen bed, 1 dual shower, a full kitchen, space is private.

The whole first floor is yours in MD Columbia

Welcome to the American Dream! Our home(total 6000+ square feet) is set in a picturesque suburban neighborhood of the nation's capital. On our first floor, we have spacious two bedrooms（3 beds) ,two bathrooms , a private access, and a full complement of amenities just for you! we can have 6 quests in total! Our 1.6 acre yard is perfect for anything from a peaceful lounge to a pickup soccer game. If you have a family, welcome!

Garden Cottage

Located in a beautiful and peaceful part of Maryland our Garden Cottage offers a cute and cozy getaway. A perfect escape from the city, our cottage is nestled among some of Maryland's best farmers markets, breweries, wineries, and outdoor experiences while still being conveniently located near several small towns and Frederick, MD. If you’re looking for a longer stay but our calendar looks booked please reach out to us!

NEW| Cozy House near Metro & WashDC| Ample Parking

Beautiful and cozy house just 25 minutes from Washington DC and only 8 minutes walk from the Glenmond metro station, with large parking sufficient for 4 vehicles, it has 2 spacious bedrooms, a full bathroom, a fully equipped kitchen and a nice living room for entertainment and family enjoyment, all the comfort and convenience in one place.